Self-Assembly of Discrete Oligomers of Naphthalenediimides in Bulk and on Surfaces

Christiaan H.W.A. Corbet, Bart W.L. van den Bersselaar, Bas F.M. de Waal, Robby Reynaerts, Kunal S. Mali, Steven De Feyter, Alain M. Jonas, E.W. Meijer (Corresponding author), Ghislaine Vantomme (Corresponding author)

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Abstract

Here, we report on the synthesis of discrete oligomers of alkyl-bridged naphthalenediimides (NDIs) and study their molecular nanostructures both in bulk, in solution, and at the liquid-solid interface. Via an iterative synthesis method, multiple NDI cores were bridged with short and saturated alkyl-diamines (C3 and C12) or long and unsaturated alkyl-diamines (u2C33 to u8C100) at their imide termini. The strong intermolecular interaction between the NDI cores was observed by probing their photophysical properties in solution. In bulk, the discrete NDI oligomers preferentially ordered in lamellar morphologies, irrespective of whether a saturated or unsaturated spacer was employed. Moreover, both the molecular architecture as well as the crystallization conditions play a significant role in the nanoscale ordering. The long unsaturated alkyl chains lead preferably to folded-chain conformations while their saturated analogues form stretched arrangements. At the solution-solid interface, well-defined lamellar regions were observed. These results show that precision in chemical structure alone is not sufficient to reach well-defined structures of discrete oligomers, but that it must be combined with precision in processing conditions.

Original languageEnglish
Article numbere202303107
Number of pages10
JournalChemistry - A European Journal
Volume30
Issue number8
Early online date27 Nov 2023
DOIs
Publication statusPublished - 7 Feb 2024

Funding

The work received funding from the Belgian National Fund for Scientific Research (EOS Project Precision 30650939), European Research Council (H2020‐EU.1.1., SYNMAT project, ID 788618), the Dutch Ministry of Education, Culture and Science (Gravitation Program 024.001.035 and NWO‐M grant OCENW.M20.256), KU Leuven (C14/19/079), and the Research Foundation – Flanders (G0H2122N, EOS 30489208).

FundersFunder number
European Research CouncilH2020‐EU.1.1, 788618
Fonds De La Recherche Scientifique - FNRS30650939
Fonds Wetenschappelijk OnderzoekG0H2122N, EOS 30489208
Ministerie van Onderwijs, Cultuur en WetenschapOCENW.M20.256, 024.001.035
Katholieke Universiteit LeuvenC14/19/079

    Keywords

    • Liquid-solid interface
    • nanostructure
    • naphthalenediimide
    • oligomer
    • self-assembly

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